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[ CAS No. 1154579-82-4 ]

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Chemical Structure| 1154579-82-4
Chemical Structure| 1154579-82-4
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Product Details of [ 1154579-82-4 ]

CAS No. :1154579-82-4 MDL No. :MFCD08063095
Formula : C11H14BF2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :241.04 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1154579-82-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1154579-82-4 ]

  • Downstream synthetic route of [ 1154579-82-4 ]

[ 1154579-82-4 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 89402-43-7 ]
  • [ 73183-34-3 ]
  • [ 1154579-82-4 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine; In 1,4-dioxane; at 80℃; for 10h; 1) Preparation of 5-(2,2-diethoxyethoxy)-2,3-difluoropyridine A 1,4-dioxane solution (30 ml) of tris(dibenzylideneacetone)dipalladium(0) (115 mg, 0.20 mmol) and tricyclohexyl phosphine (135 mg, 0.48 mmol) was degassed, then stirred at room temperature for 30 minutes. To the reaction solution, added were bis(pinacolato)diboron (1.87 g, 7.36 mmol), potassium acetate (985 mg, 10.0 mmol) and <strong>[89402-43-7]5-chloro-2,3-difluoropyridine</strong> (1.0 g, 6.69 mmol), then degassed and stirred at 80°C for 10 hours. The reaction solution was cooled to room temperature, water was added, the insoluble matter was separated by filtration, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated saline water, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product (2.6 g) containing 2,3-difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine as an orange oil.
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; tricyclohexylphosphine; In 1,4-dioxane; at 85℃; for 16h;Inert atmosphere; A mixture of of tris(dibenzyIideneacetone)dipalladium(0) (185 mg, 0.200 mmol) and tricyclohexyl phosphine (135 mg, 0.480 mmol), bis (pinacolato)diboron (1.95 g, 7.69mmol), potassium acetate (985 mg, 10.0 mmol) and <strong>[89402-43-7]5-chloro-2,3-difluoropyridine</strong> (1.00 g, 6.69 mmol) in 1 ,4-dioxane solution (30 mL) was bubbled with nitrogen and stirred at 85 °C for 16 h under nitrogen. The reaction mixture was diluted with water was added, filtered and extracted with ethyl acetate. Combined organic portions were washed with saturated saline water, then dried over anhydrous sodium sulfate and concentrated. The crude product (2.8 g) was obtained as orange oil. LC-MS (ESI): m/z 160 [M - H]"; 0.82 min (ret time).
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; tricyclohexylphosphine; In 1,4-dioxane; at 85℃; for 16h;Inert atmosphere; D42 2,3-difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) pyridine A mixture of of tris(dibenzylideneacetone)dipalladium(0) (185 mg, 0.200 mmol) and tricyclohexyl phosphine (135 mg, 0.480 mmol), bis(pinacolato)diboron (1.95 g, 7.69 mmol), potassium acetate (985 mg, 10.0 mmol) and <strong>[89402-43-7]5-chloro-2,3-difluoropyridine</strong> (1.00 g, 6.69 mmol) in 1,4-dioxane solution (30 mL) was bubbled with nitrogen and stirred at 85° C. for 16 h under nitrogen. The reaction mixture was diluted with water was added, filtered and extracted with ethyl acetate. Combined organic portions were washed with saturated saline water, then dried over anhydrous sodium sulfate and concentrated. The crude product (2.8 g) was obtained as orange oil. LC-MS (ESI): m/z 160 [M-H]-; 0.82 min (ret time).
  • 2
  • [ 1154579-82-4 ]
  • [ 1154579-85-7 ]
YieldReaction ConditionsOperation in experiment
With dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 2h; 19.2 Hydrogen peroxide water (1.37 ml, 13.4 mmol) was added to a tetrahydrofuran solution (15 ml) of the crude pyridine product (2.6 g) obtained in the above, and stirred at room temperature for 2 hours. Water was added to the reaction solution, and extracted with ethyl acetate. The organic layer was washed with aqueous 5 % sodium thiosulfate solution and saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (Biotage, hexane:ethyl acetate = 5:1 to 3:1) to obtain an yellow gum (1.0 g) containing 5,6-difluoropyridin-3-ol.
With dihydrogen peroxide In tetrahydrofuran at 20℃; for 2h; A mixture of hydrogen peroxide water (1.50 mL, 13.2 mmol) and 2,3-difluoro-5-(4,4,5,5-tetrame- thyl-l,3,2-dioxaborolan-2-yl)pyridine (2.8 g) in tetrahydrofuran (15 mL) was stirred at room temperature for 2 h, then diluted with water and extracted with ethyl acetate. Combined organic portions were washed with aqueous 5% sodium thiosulfate solution and saturated saline water, dried over anhydrous sodium sulfate and concentrated. Purification via Biotage Spla HPFC system (C18, mobile phase: 0.01% NH4HCO3, CH3CN/water, 10-95%) afforded the title product as a white solid (450 mg). LC-MS (ESI): m/z 130 [M - H]" ; 1.12 min (ret time).
450 mg With dihydrogen peroxide In tetrahydrofuran; water at 20℃; for 2h; 43 5,6-difluoropyridin-3-ol D43 5,6-difluoropyridin-3-ol A mixture of hydrogen peroxide water (1.50 mL, 13.2 mmol) and 2,3-difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.8 g) in tetrahydrofuran (15 mL) was stirred at room temperature for 2 h, then diluted with water and extracted with ethyl acetate. Combined organic portions were washed with aqueous 5% sodium thiosulfate solution and saturated saline water, dried over anhydrous sodium sulfate and concentrated. Purification via Biotage Spla HPFC system (C18, mobile phase: 0.01% NH4HCO3, CH3CN/water, 10˜95%) afforded the title product as a white solid (450 mg). LC-MS (ESI): m/z 130 [M-H]-; 1.12 min (ret time).
  • 3
  • [ 851386-35-1 ]
  • [ 73183-34-3 ]
  • [ 1154579-82-4 ]
YieldReaction ConditionsOperation in experiment
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In dimethyl sulfoxide; at 100℃;Inert atmosphere; To a 100 ml round bottom flask was charged with <strong>[851386-35-1]2,3-difluoro-5-iodopyridine</strong> (1.0 g, 4.15 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi- l ,3,2-dioxaborolane (1.16 mmol), potassium acetate (1.22 g, 12.45 mmol), Pd(dppf) (0.304 g, 0.415 mmol) in DMSO. The mixture was degassed and purged with N2 for 10 min and stirred at 100° C overnight. Mixture was washed with water and extracted with EtOAc 3x, organics dried over MgS04, filtered and concentrated in vacuo. The crude was purified by MPLC with 0-35percentHexane/EtOAc to afford product 2,3-difluoro-5-(4,4,5,5-tetramethyl- l ,3,2-dioxaborolan-2- yl)pyridine.
  • 4
  • [ 1154579-82-4 ]
  • 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine [ No CAS ]
  • C11H4F5N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
100 mg With potassium phosphate; bis(tri-tert-butylphosphine)palladium(0) In 1,4-dioxane; water at 80℃; for 16h; Inert atmosphere; 80 Synthesis of A-106: A mixtue of A-105 (324.91 mg, 1.35 mmol), A-72 (200 mg, 0.90 mmol), Pd(i-Bu3P)2 (91.85 mg, 0.18 mmol) and K3P04 (381.56 mg, 1.8 mmol) in 1,4-dioxane (10 mL) and water (2 mL) was stirred at 80 C for 16 hours under N2. After cooling to room temperature, the mixture was concentrated to give the crude product, which was purified by flash chromatography on silica gel (EtOAc in PE = 0 to 30% ) to afford A-106 (100 mg, 0.32 mmol) as a solid. 1H NMR (400MHz CDC13) _ = 9.62 (d, 1H), 8.58 (s, 1H), 8.48 (s, 1H), 8.31 - 8.24 (m, 1H). LCMS R, = 0.74 min using Method B, MS ESI calcd. for C11H5F5N5 [M+H]+ 302.0, found 301.8.
  • 5
  • [ 1154579-82-4 ]
  • 6-chloro-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyrazine [ No CAS ]
  • C15H9F6N5O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium phosphate; bis(tri-tert-butylphosphine)palladium(0) / 1,4-dioxane; water / 16 h / 80 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / 1,4-dioxane / 2 h / 0 - 20 °C
  • 6
  • [ 40971-95-7 ]
  • [ 1154579-82-4 ]
  • C11H4F5N5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
250 mg With potassium phosphate; bis(tri-tert-butylphosphine)palladium(0) In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere; 87 Synthesis of A-111: A mixture of A-1 (200 mg, 0.90 mmol), 2,3-difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (281.59 mg, 1.17 mmol), Pd(i-Bu3P)2 (91.85 mg, 0.18 mmol) and K3PO4 (381.56 mg, 1.8 mmol) in 1,4-dioxane (10 mL) and water (1.5 mL) was stirred at 90 C for 16 hours under N2. After cooling to room temperature, the mixture was concentrated to give the crude product, which was purified by flash chromatography on silica gel (EtOAc in PE = 0 to 50% to 100%) to afford A-111(250 mg, 0.83 mmol) as a solid. H NMR (400MHz, CDCI3) _ = 8.62 (s, 1H), 8.42 (d, 1H), 8.32 (dt, 1H), 7.77 (d, 1H). LCMS R, = 0.76 min using Method B, MS ESI calcd. for C11H5F5N5 [M+H]+ 302.0, found 301.9.
  • 7
  • [ 40971-95-7 ]
  • [ 1154579-82-4 ]
  • C15H9F6N5O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium phosphate; bis(tri-tert-butylphosphine)palladium(0) / 1,4-dioxane; water / 16 h / 90 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / 1,4-dioxane / 2 h / 0 - 20 °C
  • 8
  • 5-bromo-2,3-difluoropyridine [ No CAS ]
  • [ 73183-34-3 ]
  • [ 1154579-82-4 ]
YieldReaction ConditionsOperation in experiment
2200 mg With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 90℃; for 16h; 80 Synthesis of A-105: A mixture of 5-bromo-2,3-difluoro-pyridine (2 g, 10.31 mmol), 4,4,5, 5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (3.4 g, 13.4 mmol), Pd(dppf)Cl2.CH2Cl2 (1.26 g, 1.55 mmol) and KOAc (2.02 g, 20.62 mmol) in 1,4-dioxane (100 mL) was stirred at 90 C for 16 hours. After cooling to room temperature, the mixture was filtered through silica gel and eluted with EtOAc (50 mL x 2). The mixture was concentrated and diluted with EtOAc (150 mL), washed with water (100 mL x 2) and brine (80 mL), dried over Na2S04, filtered and concentrated to give the crude product, which was purified by flash chromatography on silica gel (EtOAc in PE = 0 to 10%) to afford A-105 (2200 mg, 2.32 mmol) as a solid. LCMS Rt = 0.88 min using Method B, MS ESI calcd. for CnHi5BF2N02 [M+H+2]+ 242.1, found 242.0
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